Methyl iodide → HCID 11173178, compound

HRID 843236Notes

Reaction equation

HRID 843236 reaction equation
[CH3:1][C:2]1[C:10]2[NH:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:17]([O-:19])=[O:18])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.[C:24]([O-])(O)=O.[Na+]>C1COCC1>[CH3:24][N:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:10]=2[N:9]=[C:8]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178423936HCID 178423936, compound

Product 1

HCID 11173178HCID 11173178, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution 4-methyl-2-(2-nitrophenyl)-benzimidazole (5.06 g, 20 mmol) in THF (50 mL) was added to a stirring suspension of NaH (1.2 g, 60% dispersion in mineral oil, 30 mmol) in THF (50 mL) at 0° C. under N2. The mixture was stirred at 0° C. for 30 min. and was then allowed to warm to r.t. for 1 h to form a orange solution. MeI (8.52 g, 60 mmol) was transfered into the above mixture dropwisely by a cannular at r.t under N2. This mixture was stirred for 24 h under N2 to result in a pale yellow solution. Saturated NaHCO3 (100 mL) was added. The water layer was extracted with CHCl3, the combined extracts was washed with brine, dried over Na2SO4. After removing of solvent, the residue was purified by column chromatography on silica gel using a mixture of hexane/ethyl acetate (1:1) as the eluent to give N-methyl-4-methyl-2-(2-nitrophenyl)-benzimidazole (3.0 g, 58%) as a yellow needle crystal. Rf=0.21 (hexane/ethyl acetate 1:1); 1H NMR (300 MHz, CDCl3) δ 2.68 (s, 3H), 3.60 (s, 3H), 7.12 (m, 1H), 7.26 (m, 2H), 7.65-7.80 (m, 3H), 8.23 (d, J=7.9 Hz, 1H). HRMS: Calcd for C15H13N3O2 267.1007, found 267.1007.

Workup

  1. temperatureto warm to r.t. for 1 h
  2. customto form a orange solution
  3. stirringThis mixture was stirred for 24 h under N2
  4. customto result in a pale yellow solution
  5. extractionThe water layer was extracted with CHCl3
  6. washthe combined extracts was washed with brine
  7. dry with materialdried over Na2SO4
  8. customAfter removing of solvent
  9. customthe residue was purified by column chromatography on silica gel using
  10. additiona mixture of hexane/ethyl acetate (1:1) as the eluent

Sources & evidence

ORD record
ord-09b4f04ca59e49b68464192f50044f67
Source dataset
uspto-grants-2002_04
Patent number
US06376664B1

Reaction notes

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